Trimethylsilyl cyanide → HCID 14181182, compound

HRID 1608048Notes

Reaction equation

HRID 1608048 reaction equation
O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH:5]=[CH:4][C:3]1=2.C[Si]([C:22]#[N:23])(C)C>B(F)(F)F.Cl>[C:22]([C:2]1[C:3]2[CH:4]=[CH:5][C:6]([O:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[CH:7][C:8]=2[CH2:9][CH2:10][CH:11]=1)#[N:23]

Participants

5

Reactant 2

HCID 82115Trimethylsilyl cyanideHCID 14181181HCID 14181181, compound

Product 1

HCID 14181182HCID 14181182, compound

Reagents, catalysts & solvents 2

HCID 6356Boron trifluorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

2 to 3 drops of BF3 -etherate solution are added to 0.1 mol of methyl 5-oxo-5,6,7,8-tetrahydro-naphth-2-yl-oxyacetate and 0.15 mol of trimethylsilyl cyanide, and the mixture is stirred at room temperature for 30 minutes and then at 50° C. for 1 hour. 250 ml of a saturated methanolic hydrogen chloride solution are added to this solution at room temperature and the mixture is stirred for 1 hour. Some of the product precipitates out and is filtered off. A further batch is obtained by evaporating the mother liquor, taking up the residue in CH2Cl2, extracting the mixture twice by shaking with 0.5N NaOH, drying the extract over Na2SO4 and evaporating it and recrystallizing the residue from a little methanol or diisopropyl ether.

Workup

  1. waitat 50° C. for 1 hour
  2. stirringthe mixture is stirred for 1 hour
  3. customSome of the product precipitates out
  4. filtrationis filtered off
  5. customA further batch is obtained
  6. customby evaporating the mother liquor
  7. extractionextracting the mixture twice
  8. stirringby shaking with 0.5N NaOH
  9. customdrying the
  10. extractionextract over Na2SO4
  11. customevaporating it
  12. customrecrystallizing the residue from a little methanol or diisopropyl ether

Sources & evidence

ORD record
ord-225ea5388bd34c67a158ece24ed177f3
Source dataset
uspto-grants-1989_09
Patent number
US04868332

Reaction notes

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